1. Technical Field of the Invention
This invention relates to the modification of elastomers with dienes and more particularly to polyoxyalkylene amines and the reaction thereof with an isocyanate to form new compositions generally useful in cross-linking vinyl monomers. The composition exhibits advantages over similar products prepared from polyols and isopropenyl dimethylbenzyl isocyanate.
A wide range of polyoxyalkylene amines may be employed. JEFFAMINE.RTM. EDR-series amines, for example, are reacted with isopropenyl dimethylbenzyl isocyanate to form solid olefin-terminated polyoxyalkylene amine ureas. In another embodiment polyoxyalkylene diamines, such as JEFFAMINE.RTM. D-series and EDR-series amines are reacted with isopropenyl dimethylbenzyl isocyanate to form olefin-terminated polyoxyalkylene diamine ureas which are generally solids except for the case where the high molecular weight JEFFAMINE.RTM. D-2000 amine is the reactant.
2. Related Art
It is known in the art to use some dienes to modify the properties of elastomers via heat, ultraviolet, peroxide and Ziegler type catalyst curings or polymerization. For example, the ethylene propylene diene elastomer is a polymer made by such a technique.
Work in the field of copolymerization of this type is described in an article titled "Synthesis of EPDM Elastomer By Fluid Bed Processing" PERP Quarterly Report, Vol. 4, 1985. This article contains a very good overview of the history of ethylene propylene rubbers and provides an analysis of one method to produce low density, low modulus ethylene copolymers in a fluidized bed using a diene. It is noted that in that fluid bed process the use of a catalyst is necessary, such as an organo-metallic of the Ziegler type catalyst.
In U.S. Pat. No. 4,618,652 there is disclosed a method of thermally curing a bismaleimide resin into a solid polymer by admixing a small amount of 5-vinyl-2-stilbazole as the copolymeric unit. It is stated that the properties of bismaleimide resins and their preparation conditions are substantially improved by this method. No catalysts were used in the preparation of the copolymers.
In an article titled "1,5-Hexadiene and 1,9-Decadiene: New Specialty Chemicals", Chemical Systems PERP Quarterly Report, Vol. 3, 1985, there is described another application of the metathesis reaction, the interaction of cyclic olefins with ethylene to provide alpha, omega-dienes. Here, 1,5-hexadiene is obtained by the reaction of ethylene with the butadiene dimer, 1,5-cyclooctadiene, and 1,9-decadiene results from the reaction of ethylene and cyclooctene. These materials are regarded as specialty multifunctional olefins for use in cross-linking ethylene and propylene elastomers.
In the art discussed above there does not appear to be anything which would suggest the production of olefin-terminated ureas from polyoxyalkylene amines.
It would be desirable if novel high molecular weight diolefin compounds for copolymerization could be prepared. It would be very desirable if these novel olefin compounds could be used in a number of olefin polymerizations or to modify properties of elastomers without the addition of organometallic or tertiary amine catalysts via heat or free radical initiators. Further, it would be advantageous if the compositions resulting from use of these compounds in copolymerization exhibited desirable properties.